Long before Chicago played a note, we spent the afternoon wandering the fairgrounds, doing exactly what generations of San Diegans have done every summer for a century. We admired prize-winning livestock. We strolled through the flower exhibits. We marveled at woodworking creations that looked impossible to make by hand. We studied photographs and paintings from talented local artists. We ate ridiculous fair food. We watched children sprint toward carnival rides with the same excitement kids have carried through these gates for decades.
There is something deeply comforting about the fair. In a world increasingly dominated by screens, algorithms, notifications, and endless digital distraction, the fair remains stubbornly human. It is chaotic and imperfect and noisy. It smells like barbecue, funnel cakes, livestock, sunscreen, and nostalgia. It feels like America.
At one point we grabbed one of this year's viral food creations - the Blueberry Brie Smash Dog served on a buttery croissant - and headed to Destination Unknown, the hidden sixth-floor speakeasy overlooking the fairgrounds. Cocktails in hand, we watched the midway begin to glow as the sun slowly sank toward the Pacific.
Then it was time for Chicago. And what a setting. The Corona Grandstand Stage may be one of Southern California's more underrated concert venues. Set alongside the Del Mar racetrack, with carnival lights flickering in the distance and a giant Ferris wheel illuminating the evening sky behind the stage, it creates the feeling that you've somehow stumbled into a perfect summer memory while it's happening.
Chicago understood the assignment immediately. Opening with "Dialogue" and then launching into "Does Anybody Really Know What Time It Is?," the band wasted no time reminding the audience why they remain one of the most successful and enduring acts in American music history.
The crowd, remarkably energetic for a Wednesday night, responded instantly. One of the evening's biggest surprises was just how powerful Chicago sounds in 2026.
Then it was time for Chicago. And what a setting. The Corona Grandstand Stage may be one of Southern California's more underrated concert venues. Set alongside the Del Mar racetrack, with carnival lights flickering in the distance and a giant Ferris wheel illuminating the evening sky behind the stage, it creates the feeling that you've somehow stumbled into a perfect summer memory while it's happening.
Chicago understood the assignment immediately. Opening with "Dialogue" and then launching into "Does Anybody Really Know What Time It Is?," the band wasted no time reminding the audience why they remain one of the most successful and enduring acts in American music history.
The crowd, remarkably energetic for a Wednesday night, responded instantly. One of the evening's biggest surprises was just how powerful Chicago sounds in 2026.
With only a handful of original members remaining, lesser bands often become tribute acts to themselves. Chicago has somehow avoided that fate. The current lineup feels less like a nostalgia act and more like a living continuation of the band's legacy.
Founding members Lee Loughnane, James Pankow, and Robert Lamm remain extraordinary performers whose presence still anchors the group. Their contributions helped build one of the most distinctive sounds in rock history, and hearing those legendary horn arrangements performed by musicians who helped create them remains a privilege.
At the same time, newer members have elevated the band's current incarnation into something genuinely impressive. The horn section remains razor sharp. The rhythm section hits with surprising force. Guitarist Tony Obrohta and bassist Eric Baines provide energy and precision throughout the performance. Walfredo Reyes Jr. and Ramon Yslas keep everything moving with effortless confidence.
Founding members Lee Loughnane, James Pankow, and Robert Lamm remain extraordinary performers whose presence still anchors the group. Their contributions helped build one of the most distinctive sounds in rock history, and hearing those legendary horn arrangements performed by musicians who helped create them remains a privilege.
At the same time, newer members have elevated the band's current incarnation into something genuinely impressive. The horn section remains razor sharp. The rhythm section hits with surprising force. Guitarist Tony Obrohta and bassist Eric Baines provide energy and precision throughout the performance. Walfredo Reyes Jr. and Ramon Yslas keep everything moving with effortless confidence.
But the revelation of the night was Rudy Cardenas. Chicago's newest lead vocalist possesses the nearly impossible ability to honor the band's classic recordings without merely imitating them. His voice carries warmth, power, and familiarity, often sounding remarkably close to the original recordings while still feeling entirely authentic. It would be difficult to imagine a better fit.
As darkness settled over the fairgrounds, the evening became increasingly magical. "You're the Inspiration" arrived just as the sky turned shades of orange, purple, and deep blue. Couples wrapped their arms around each other. Phone lights illuminated the crowd. The Ferris wheel glowed behind the stage. It was one of those moments that reminds you why live music matters.
"Saturday in the Park" felt particularly appropriate given the surroundings. Thousands of people had spent the day eating, laughing, riding rides, and making memories just beyond the grandstand walls. The song became less a performance and more a celebration of the very thing everyone had come to experience. By the time Chicago launched into "Feelin' Stronger Every Day," "Old Days," and the night's explosive finale, "25 or 6 to 4," the audience was fully invested.
As darkness settled over the fairgrounds, the evening became increasingly magical. "You're the Inspiration" arrived just as the sky turned shades of orange, purple, and deep blue. Couples wrapped their arms around each other. Phone lights illuminated the crowd. The Ferris wheel glowed behind the stage. It was one of those moments that reminds you why live music matters.
"Saturday in the Park" felt particularly appropriate given the surroundings. Thousands of people had spent the day eating, laughing, riding rides, and making memories just beyond the grandstand walls. The song became less a performance and more a celebration of the very thing everyone had come to experience. By the time Chicago launched into "Feelin' Stronger Every Day," "Old Days," and the night's explosive finale, "25 or 6 to 4," the audience was fully invested.
People weren't heading for the exits when the show ended. They were heading back into the fair. Back to the midway lights. Back to the carnival games. Back to the rides. Back to one more snack they absolutely didn't need. Back to summer.
After the concert, we wandered through the fairgrounds once again, played games, rode rides, and I somehow won an enormous stuffed animal for Lady SanDiegoVille. Across the property, Blue Öyster Cult was performing a free concert in the Paddock, creating a one-two punch of classic rock that felt uniquely fair-like in the best possible way.
And that's ultimately what makes nights like this so special. The San Diego County Fair isn't really about livestock or rides or food or concerts. It's about remembering. Remembering what it felt like to be young. Remembering that joy doesn't always need a purpose. Remembering that sometimes the best nights aren't carefully planned luxury experiences but simple evenings spent wandering with someone you love.
Chicago provided the soundtrack. The fair provided the setting. Together, they created something far more meaningful than a concert. They created a memory.
And in a world moving increasingly fast, that's becoming one of the most valuable things any of us can take home.
And that's ultimately what makes nights like this so special. The San Diego County Fair isn't really about livestock or rides or food or concerts. It's about remembering. Remembering what it felt like to be young. Remembering that joy doesn't always need a purpose. Remembering that sometimes the best nights aren't carefully planned luxury experiences but simple evenings spent wandering with someone you love.
Chicago provided the soundtrack. The fair provided the setting. Together, they created something far more meaningful than a concert. They created a memory.
And in a world moving increasingly fast, that's becoming one of the most valuable things any of us can take home.
The San Diego County Fair takes place through July 5, 2026. Check out our Ultimate Guide To The 2026 San Diego County Fair for more information.
Originally published on June 11, 2026.
